What to Wear to Work

The Esquire Guide to Dressing for the New Office

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Jan 29, 2007

You're in one of those of those white-shoe law firms that this last summer finally announced it was changing its dress code from suits-only to more-casual clothes. And now, without your trusty two-piece, you don't know what to do.

Or maybe you're just sick of the khakis and polo shirt you've been wearing to your I.T. office since that first dress-down Friday back in 1995. Who can blame you? That once-fine weekend outfit has pretty much evolved into the same uniform the navy-blue suit and red power tie used to be--it's found in nine out of ten cubicles.

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Whoever you are, whatever kind of company you work in, there is another way--a more stylish, more professional way. We call it dressing for the new office, and though it doesn't shun the khakis and polo, it most definitely includes the suit and just about every combination of sensible clothing in between. You see, it's not about dressing down, this whole revolution. Dressing down is what you do when you're going to clean out the garage. What we're talking about here is dressing up. Dressing up, only a little less formally, perhaps a little more creatively, than you once might have. You see, while the rules of the new office may have changed--less obvious hierarchy, no real stability--the rules for looking good remain the same.

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Let us explain. There are three main principles of dressing for the new office, and they're pretty much the same as those that applied (or should have applied) to the old office. One, you want clothes made from quality materials--fine, soft fabrics that befit a man of stature. Two, you want them to be constructed with excellent craftsmanship: You expect nothing less in your car; why compromise with your clothes, which you inhabit for far more hours each day? Three, you want them to fit well and be clean--that one, that should be self-explanatory. Simple, right? Think of these nuggets as the requisite knowledge for the rest of this section, a short course in style that allows you to appear creative to the Web designers while showing the CEO he can have confidence in your ability to manage the IPO--without having to change. On the following pages, you'll find twenty pieces of clothing--they represent the goods you'll want to hang in your new-office closet. They're followed by the accessories to go with them, a handful of rules on how to put it all together, and then the final results. Read. Study. Practice. Wear. And remember: You could do worse. Every single day in America, most men do do worse. Of course, with our help, you don't have to.

The Twenty-Piece Closet

HOW MANY CLOTHES do you need? Not as many as you think, provided they are the right clothes. These, for example. The succinct collection arrayed here contains the threads we'd pick if one day we had to start a proper day job. These modern pieces not only strike the right balance between formal and informal, but they also pretty much all coordinate with one another. That means the savvy man can put together dozens of outfits, from a serious suit-and-tie look to something for a trip to a trendy club--wherever work (and whatever comes after) may take him, which, let's hope, is far.

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This navy pinstripe suit's specialness stems from a more narrow-gauge stripe than the ones favored by old-economy types. That makes it modern while still allowing it to function as the foundation of the dressiest outfit you'll need for the new office. A gray suit is also a good bet. This reasonably priced model is cut from a wrinkle-resistant stretch material, which makes it travel friendly.

A car coat in a sophisticated, supple leather is the perfect topper for the new-office wardrobe, thanks to its versatility. It looks as smart over a sleek suit as it does with pinstripe trousers and a turtleneck.

A softly constructed Donegal-tweed sport coat--this one very lightweight--brings a touch of the country to the office wardrobe. The subtle glen-plaid sport coat is unlined and soft, almost like a tailored sweater. They both offer comfort in the guise of serious tailored pieces.

Three pairs of trousers--no khakis. Does that make you nervous? Or thrilled? If you don't want to look like everyone else, say thrilled. The small-wale cord, left, the substantial brushed cotton, and the versatile light-gray wool trousers (all of which are in the more modern flat-front style) will keep you covered as well as any chain-store khakis--but a whole lot more stylishly.

Shiny, flat ties work well with traditional shirts and suits, but the varied fabrics in the new wardrobe require neckties that have some texture. Three will do you just fine: a patterned matte-silk number, center, and two wool jobs, which match nicely with more-substantial shirts and sweaters.

Button-down shirts in patterned fabrics and hefty weaves have none of the stiffness of the white straight-collared numbers once worn by white straight-collared numbers. You need a couple of them. You also need something like the two shirts at top right. They've got tie-worthy spread collars, but they're constructed in such a way that once their top buttons are unfastened, they lose their formality and open like a fine casual shirt. That's adaptability, a key quality in your wardrobe and, most likely, in your office.

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An assortment of sweaters will provide a man not only with warmth but also with a range of options. The cable-knit turtleneck is fine enough to wear under a sport coat, for example. The polo and crewneck can be worn likewise, either solo or over a shirt or a shirt and tie. The V-neck works that way, too, since its V is not so deep you'd ever show off your--warning! warning!--chest hair. Meanwhile, the zipper on the gray sweater offers a note of modernity.

The Essential Extras

Time was you could distinguish the big shots by the suits they wore. Now, with fewer of any kind of shots wearing suits, that's harder to do. Of course, it's harder for you to distinguish yourself, too. At least until you discover the impact quality accessories can have on your appearance. For example, a man looks most polished when his shoes are polished, meaning they should be leather and lace up and not be the kind endorsed by athletes. We like the cap-toe lace-ups and boots on this page and the traditional black wing tips, all of which are less fusty than plain-toe kicks but still dressy. A man also looks good when his belt matches his shoes in color, if not in material. One each in brown and black calfskin is all you really need to keep your pants up. And then there are bags. Bags need to be appropriate to the formality of your outfit, which pretty much means you shouldn't be toting the Bigsby files to the office in a Wal-Mart shopping bag no matter how casually you're dressed. Instead think about these: an informal canvas messenger bag, a slightly more formal attaché, and a sleek but still not hard-sided or stodgy black shoulder bag. And finally, there's the watch, which should never beep or be plastic. Try a classic leather-band tank and a more modern metal number. Not only will they signal to the discerning colleague what kind of man you are, but they'll be good investments, too, capable of appreciating in value as time goes by.

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The Rules

WHEN A COMPANY CAN LOSE MONEY FOR SIXTEEN STRAIGHT QUARTERS and still have a multi-billion-dollar market cap, it might seem that rules--not to mention common sense--no longer apply. And maybe in the high-tech sector, such things don't. But in the realm of style, well, there are still guidelines. Below, you'll find some of the most important ones. Adhere to them and, whichever way the Nasdaq trends, your stock will never fall.

Do you remember how people used to say that you should dress not for the job you have but for the one you want? That is still true.

What that means: Though you may not be required to wear a gray chalk-stripe suit, you still need to demonstrate some respect not only for yourself but also for the seriousness with which you take your work.

Ergo, suits are not forbidden.

In fact, the suit and sport jacket remain the primary foundation of the so-called office-casual wardrobe. They keep you warm, offer plenty of pockets, and provide you with the right measure of dignity upon receiving that unexpected promotion. Or pink slip.

Sport jackets require trousers that are not the informal, unpressed khakis you wear with a T-shirt on weekends.

The chinos that are right for the office: clean-cut versions in heavier and higher-quality fabrics. Cool-weather alternatives: brushed cotton, moleskin, corduroy.

A RELAXED DRESS CODE DOES NOT LEGITIMIZE THE DISPLAY OF LEG HAIR OR CHEST HAIR.

No T-shirts. No sneakers.

Shorts in the office: only if your office is a wooden chair mounted atop a ladder on a sunny beach and a whistle hangs from around your neck.

Likewise, you do not dress for the office as you would for the golf course.

The big-day-in-court briefcase is inappropriate for the turtleneck-sweater day at the office.

Multicolored, multipatterned sweaters are for the taping of infomercials.

Keep your color selection simple: blues, grays, browns, and camels, for example. This allows all the pieces of your wardrobe to be coordinated with ease.

More vivid colors, which are useful as accents, should not be overly sporty or garish: Start with french blue, dark green, butterscotch.

Sport jackets should be as comfortable as knitwear, featuring soft, natural shoulders, light or no lining in lightweight fabrics.

THE NEW SUITS IN YOUR WARDROBE SHOULD BE VERY VERSATILE--THAT IS, YOU SHOULD BE ABLE TO WEAR THE JACKET AND THE PANTS SEPARATELY. PATCH POCKETS, SOFT MATERIALS, EASY CONSTRUCTION, AND PLAIN-FRONT PANTS FACILITATE THIS.

Knitwear can be key in making any outfit more casual and relaxed. Under the suit, try lightweight sweaters or knitted vests or cardigans in such noble yarns as merino wool, cashmere, or alpaca.

A cardigan can substitute for a jacket.

One good reason to always dress better for work than you otherwise might: People won't assume you have a job interview elsewhere on those days you dress nicely because you do, in fact, have a job interview elsewhere.

T-shirts, though--they tilt perilously in the direction of Miami Vice.

LEATHER BLAZER: ONLY IF YOUR OFFICE IS A CADILLAC AND YOUR BOSS IS A SOPRANO.

What jeans are for: car washing, baseball-game attending, crab boiling, et cetera. Ditto sneakers. Was office casual listed among the aforementioned activities that jeans and sneakers are for? It was not.

Would anybody mind if we quietly pointed out again the important fact that what we're doing here is getting dressed to go to work?

Therefore, it is still necessary to shave.

Crucial factor in selecting one's office-casual attire: whether one deals with members of the general public.

Times when one might revert to more-traditional attire: new-client meetings, formal presentations, days when one plans to fire somebody's ass.

Times when one might opt for more-relaxed gear: when chained to one's desk for days on end, acres away from anybody one might need to impress.

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Caveat: One never knows when people one needs to impress might show up unannounced.

Cable-knit sweaters in which one goes hunting or skiing or rakes leaves are not appropriate.

Belts are necessary.

Socks are necessary.

Funny socks are not only not necessary, they are forbidden.

Putting It Together

BEING A MAN OF STATURE, you know how to wear a suit with its traditional garnish of shirt and tie. Most likely with a sweater, too. It's breaking a suit's pieces down and mixing them up that can confuse. Which is why we'll gloss over the former (despite the suit's continuing importance in your wardrobe when you choose--or need--to wear it) and offer plenty of advice on the latter. Advice in the form of a one-week supply of office-worthy outfits, put together with the twenty pieces you checked out a few pages back. You'll see that a coat of some kind--either a sport coat or the jacket from a suit--figures prominently. We believe that that garment provides a man with an authoritative comportment as well as a place to put his wallet, cell phone, and Palm V. (It also does away with the need to change for an unexpected meeting.) The suit trousers get used in this manner, too, as well as a whole range of other trousers, shirts, sweaters, and neckties (which, when not noosed around a too-tight shirt collar, can be a fine way to add interest to an otherwise ordinary outfit). All of this mixing and matching stretches the value of your closet. Accountants call it amortizing, and it's the best way to smartly broaden your wardrobe without buying more clothes. Hey, whoever said bean counters weren't creative?

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MONDAY This outfit--supersoft tweed, a lofty turtleneck, and corduroys--provides the comfort a man needs to ease into the workweek. If your day calls for a little more formality, you can lose the sweater in favor of the beige button-front shirt and the tan tie. And if so much brown's not your bag, the gray suit trousers and even the zip-front sweater will work with this sport coat. Either way, the cap-toe lace-up boots and the canvas messenger bag tie it all together.

TUESDAYA major-league workday calls for a slightly more sophisticated take on the age-old casual classic of the navy sport coat. In this case, the jacket comes from the pinstripe suit, while the trousers come from the gray one. Under the jacket, we've shrugged on the zip-front sweater, but if you don't like to layer, you could just as well forget the knit and let the shirt and tie speak for you. Finally, the steely look of the metal-band watch provides the right note of don't-mess-with-me attitude for such a sharp put-together.

WEDNESDAY Running numbers with the boss, sales calls, a working lunch, and client drinks--there's a reason they call it hump day. Such a high-pressure schedule demands a no-worries outfit. Enter the uncomplicated pairing of the gray suit jacket and the brushed-cotton trousers. Here they're shown with the lightweight crewneck over a shirt, but you could wear either the shirt or the sweater alone. See, this whole new-wardrobe thing is about options--just like the ones you got with your compensation package. You did get a compensation package, didn't you?

THURSDAY The light-gray colors of this outfit provide a contrast to typically dark flannel for an image that's as fresh as the ideas you bring to the office. Note the way the polo sweater's collar stands up above the jacket lapel: Unlike most polos, it's constructed like a dress shirt, which makes it ideal for under-coat wear. This color gray, by the way, works best with the brown shoes, the brown leather watch, and a brown, sophisticated attaché, all of which are softer in feel than high-shine black.

FRIDAY While every other cubicle denizen is easing up at the end of the week, the smart man can distinguish himself with a suit, say, or at the very least this sharp look--the pinstripe suit trousers with a shirt and tie and the navy V-neck. When matched with the car coat and the sleek leather shoulder bag, it's a bonus outfit: right for work but able to take you out on the town immediately after for that all-important end-of-the-grind cocktail or three.

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The Unsuitable

WOE IS THEM, the poor souls who dressed for the new office before reading our guide to dressing for the new office. They made so many mistakes. They received so many HR memos. They gave us these funny pictures, along with a handful of anecdotes recounting all manner of war stories from the front lines of the dress-code revolution, which you will now bear in mind. Right?

For Pete's sake, man, it's an office. Dress accordingly. To wit: "The huge brokerage house in the offices downstairs went casual," one financial professional told us. "And the guys look like absolute crap." These guys, they are salesmen, the frontline people who must instill confidence in prospective clients, remember. "I can't believe they let salesmen go casual without showing them how to do it," said the finance guy. "It's not like going to freshman bio lecture; you still have to look good to sell."

It has come to this: Business attire can now be embarrassing, even in the course of business. A managing partner of a hundred-year-old law firm goes on a plant visit with an important client. A traditionalist, he wears something probably blue, possibly gray, definitely striped. And at the plant, everyone is casual but him. "Oh, my God, we forgot to tell you," the client gasps. "Whenever someone shows up in a coat and tie, employees think the company is going to be sold."

A salesman for a B2B e-outfit comes calling on a huge home-improvement chain in a southern suburb. Normally, this fella sports flannel and jeans, but today, it's a suit. This proves exactly wrong. The chain's executives wear blue jeans to work, and today, in fact, is Apron Day--the execs look just like the guy who cuts the threads on conduit. Worse: Despite the fact that this DIY giant is situated in a region where courtliness is as much a cultural imperative as grits, callers in suits are admonished as follows, not in a whisper but in front of everybody during the meeting, with no apparent regard to the astonishing rudeness and arrogance of this action: "You should know that it is inappropriate to wear a suit here." Owwwch.

Little rule of thumb: If your bag involves customers placing large sums of their hard-earned legal tender in your custody, you should bear in mind that many of said customers still prefer that you look like a trustworthy, professional sort, as opposed to someone on his way to a Phi Delt smoker. One banker remembered a colleague's failure in this department: "Big-time client invites this guy, a financial consultant, to a lunch meeting at the country club. Guy figures, knit polo shirt and creased khakis--a nice look but casual. With some clients, this might be okay, but one way or another, you must know before you go--call the secretary, ask a colleague, something. The consultant did not. Naturally, the client shows up in a three-piece, looking schwank. The consultant shrinks in his chair; he becomes a greasy puddle. He will never again wear anything but a navy-blue pinstripe--even to a barbecue."

True, the new rules may be daunting, but that does not excuse oppressive homogeneity: It is no more okay for everyone to wear the same thing to the office than it was for all the girls in high school to have the same prom dress. "Everyone around here pretty much wears khakis and a blue shirt," said one Web-site VP. "I've been to five meetings with the guy who sits in the next office, and we've both worn the same blue-checkered shirt with stone-colored khakis all five times. He now brings a sweater just in case he has to cover himself."

One investment executive figures his job takes him through enough modes (make nice with underlings, impress customers, fit in with execs) that it requires an equal number of costume changes. One day, khakis for the rank and file segued into a suit for lunch with the boys from TIAA-CREF, which morphed into a sport coat and driving shoes for a meeting with management, only to return to the suit for a client dinner. There's got to be a better way. Hopefully you've found it on these pages.